Okay – so at Step 1, we figured out at least roughly whether we ultimately want to be in a relationship and (if so) what the various midlife bachelor developmental stages are in order to achieve that type of success. We started with the basics (personal appearance and hygiene, then moved on to attitude and social skills development while minimizing one’s individual emotional baggage, then we somehow magically moved on to getting a date (ANY date), and began to work on the ability to have fun on those dates. This magical transition from working on your personal basics to “developmental dating” is what Step 2 is all about.

Developmental Dating
What I call “developmental dating” refers to your ability as a midlife bachelor to go out, and get a date with a woman … go out on that date … and actually have fun on the date. “Having fun on the date” does not necessarily equate with “having sex” – but it might. Let’s face it – as men, sex is always our goal no matter what. But - when you first start dating, if you are sincere about successfully re-entering the dating world as a midlife bachelor, then your focus should be foremost on having a nice time on any given date. A “nice time” always means that the date was a pleasant, comfortable experience for all involved. A “nice time” might sometimes mean that you are able to get yourself a good night kiss – although not always. A “nice time” might mean that you learned a lot about one another, and want to know more. A “nice time” might mean that she won’t press charges (just joking). A “nice time” can mean many things obviously – but it might NOT necessarily mean that you want to see one another again. In other words, you can have a “nice time” with someone, and not want to date them. Don’t pre-judge your success at developmental dating based on your initial ability or inability to get laid or kissed or get second dates, as dating success for a midlife bachelor is often more of an evolutionary (versus instantaneously) successful process. I’ll explain all of this so that it is clear.

When you first re-enter the midlife dating world, two of the biggest obstacles are

Getting a date

Having fun on a date you do get

First Identify a Potential Date
Just asking for a date can be a stressful experience – especially if you have not been single for quite some time. First you have to identify a woman who you want to ask out. Now this is important – the woman has to like you and/or be attracted to you. You cannot automatically assume (because of your ego) that every woman you are interested in will also be interested in you. Unless you are super good-looking, there is always some element of random chance involved that she will (or will not) recognize some potential chemistry between the two of you.

Sometimes it is easy to know that a woman is attracted to you, and maybe wants to go out. Some women are obvious – they go out of their way to either talk to you, or to notice you, or to say “hi” to you. Other women are really hard to read – and you have to keep your eyes open at all times for any hint of a possibility of a woman’s interest. Here are a couple of stories from my past concerning obvious and non-obvious women. Margie (who I also wrote about earlier) worked at a local postal retail store where I rented a mailbox. At that time, whenever I received a FEDEX or UPS package, the store would call me and ask me to come and pick it up. When I was in the store, I always spoke to several of the employees there – but Margie was a little different … she would almost never look at me in the face. She would instead look down or look away. At the time I didn’t think too much about it – and I had not really considered Margie someone who would be interested in me or vice versa. But over several months, I noticed that it was always Margie who was calling me from the store. One day, she called and I asked if I had a package to pickup … and she said “no”. I then asked her why she was calling … and she said she didn’t know, and sounded kind of embarrassed. Fortunately, I immediately picked up on what was going on, and I asked her if she wanted to have dinner … and she got all excited, and said sure. She later admitted to me that she had a huge crush on me … which I almost would not have noticed had she not called and embarrassed herself. [She said that she did not expect me to answer my home phone, and was calling to hear my voice on the answering machine.] Margie was really hard to read – even when we were dating, she had a hard time looking right at me.

Margie was really shy, and had I not busted her calling my home phone, I probably never would have recognized that she liked me. A good midlife bachelor lesson is here – always keep your eyes open. Don’t overly assume the best, but also don’t be ignorant of what may be going on. If there is any question about a woman’s intentions about you, you can always talk to her more and try to figure out whether she is just a nice person versus interested in dating you.

Margie was very non-obvious prior to the phone calls. Other women are way more obvious about liking you. You may recall my earlier story about Becky, the blonde bombshell nymphomaniac who demonstrated to me that the hottest fires burn out the quickest? I mentioned before that she and I had been “friends” for a long period of time – but now let me elaborate on that to illustrate how some women are OBVIOUS about liking you. For many years, Becky had worked at a local pharmacy as a pharmacy technician – the person who interacts with the people who need to fill or refill a prescription. I can remember in my mid-twenties seeing Becky at this pharmacy … and each of us would always say “hi” when I was in the store (whether I needed a prescription or not). We would do the small talk thing – we would tell one another about who we were dating, how that was going, etc. The point here is that she would go way out of her way to talk to me, and I would, too. It was always a friendship thing because neither one of us were ever single at the same time over the years … until fairly recently. After I was dating Becky, she told me what I essentially already knew … that for all those years, she wanted to go out with me. Of course, my very physical relationship with Becky went nuclear (no survivors) very quickly – but hey, it was fun while it lasted!